Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds
Isomorphous crystals of two diacetylene derivatives with carbamate functionality (BocNH-CH2-diyne-X, where X = H or Br) have been obtained. The main feature of these structures is the original 2D arrangement (as supramolecular sheets or walls) in which the H bond and halogen bond have a prominent ef...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2016-04-01
|
| Series: | Crystals |
| Subjects: | |
| Online Access: | http://www.mdpi.com/2073-4352/6/4/37 |
| _version_ | 1811184880632987648 |
|---|---|
| author | Pierre Baillargeon Édouard Caron-Duval Émilie Pellerin Simon Gagné Yves L. Dory |
| author_facet | Pierre Baillargeon Édouard Caron-Duval Émilie Pellerin Simon Gagné Yves L. Dory |
| author_sort | Pierre Baillargeon |
| collection | DOAJ |
| description | Isomorphous crystals of two diacetylene derivatives with carbamate functionality (BocNH-CH2-diyne-X, where X = H or Br) have been obtained. The main feature of these structures is the original 2D arrangement (as supramolecular sheets or walls) in which the H bond and halogen bond have a prominent effect on the whole architecture. The two diacetylene compounds harbor neighboring carbamate (Boc protected amine) and conjugated alkyne functionalities. They differ only by the nature of the atom located at the penultimate position of the diyne moiety, either a hydrogen atom or a bromine atom. Both of them adopt very similar 2D wall organizations with antiparallel carbamates (as in antiparallel beta pleated sheets). Additional weak interactions inside the same walls between molecular bricks are H bond interactions (diyne-H···O=C) or halogen bond interactions (diyne-Br···O=C), respectively. Based on crystallographic atom coordinates, DFT (B3LYP/6-31++G(d,p)) and DFT (M06-2X/6-31++G(d,p)) calculations were performed on these isostructural crystals to gain insight into the intermolecular interactions. |
| first_indexed | 2024-04-11T13:20:58Z |
| format | Article |
| id | doaj.art-0f5d5f95038d457d9908e20af1d65b8e |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-11T13:20:58Z |
| publishDate | 2016-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-0f5d5f95038d457d9908e20af1d65b8e2022-12-22T04:22:12ZengMDPI AGCrystals2073-43522016-04-01643710.3390/cryst6040037cryst6040037Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen BondsPierre Baillargeon0Édouard Caron-Duval1Émilie Pellerin2Simon Gagné3Yves L. Dory4Département de chimie, Cégep de Sherbrooke, 475 rue du Cégep, Sherbrooke, QC J1E 4K1, CanadaDépartement de chimie, Cégep de Sherbrooke, 475 rue du Cégep, Sherbrooke, QC J1E 4K1, CanadaDépartement de chimie, Cégep de Sherbrooke, 475 rue du Cégep, Sherbrooke, QC J1E 4K1, CanadaDépartement de chimie, Cégep de Sherbrooke, 475 rue du Cégep, Sherbrooke, QC J1E 4K1, CanadaLaboratoire de synthèse supramoléculaire, Département de chimie, Institut de Pharmacologie, Université de Sherbrooke, 3001 12e avenue nord, Sherbrooke, QC J1H 5N4, CanadaIsomorphous crystals of two diacetylene derivatives with carbamate functionality (BocNH-CH2-diyne-X, where X = H or Br) have been obtained. The main feature of these structures is the original 2D arrangement (as supramolecular sheets or walls) in which the H bond and halogen bond have a prominent effect on the whole architecture. The two diacetylene compounds harbor neighboring carbamate (Boc protected amine) and conjugated alkyne functionalities. They differ only by the nature of the atom located at the penultimate position of the diyne moiety, either a hydrogen atom or a bromine atom. Both of them adopt very similar 2D wall organizations with antiparallel carbamates (as in antiparallel beta pleated sheets). Additional weak interactions inside the same walls between molecular bricks are H bond interactions (diyne-H···O=C) or halogen bond interactions (diyne-Br···O=C), respectively. Based on crystallographic atom coordinates, DFT (B3LYP/6-31++G(d,p)) and DFT (M06-2X/6-31++G(d,p)) calculations were performed on these isostructural crystals to gain insight into the intermolecular interactions.http://www.mdpi.com/2073-4352/6/4/37isomorphismcrystal structuressupramolecular sheetshydrogen bondhalogen bondsynthesisdiacetylenebromodiyneterminal alkyneDFT theoretical calculation |
| spellingShingle | Pierre Baillargeon Édouard Caron-Duval Émilie Pellerin Simon Gagné Yves L. Dory Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds Crystals isomorphism crystal structures supramolecular sheets hydrogen bond halogen bond synthesis diacetylene bromodiyne terminal alkyne DFT theoretical calculation |
| title | Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds |
| title_full | Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds |
| title_fullStr | Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds |
| title_full_unstemmed | Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds |
| title_short | Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds |
| title_sort | isomorphous crystals from diynes and bromodiynes involved in hydrogen and halogen bonds |
| topic | isomorphism crystal structures supramolecular sheets hydrogen bond halogen bond synthesis diacetylene bromodiyne terminal alkyne DFT theoretical calculation |
| url | http://www.mdpi.com/2073-4352/6/4/37 |
| work_keys_str_mv | AT pierrebaillargeon isomorphouscrystalsfromdiynesandbromodiynesinvolvedinhydrogenandhalogenbonds AT edouardcaronduval isomorphouscrystalsfromdiynesandbromodiynesinvolvedinhydrogenandhalogenbonds AT emiliepellerin isomorphouscrystalsfromdiynesandbromodiynesinvolvedinhydrogenandhalogenbonds AT simongagne isomorphouscrystalsfromdiynesandbromodiynesinvolvedinhydrogenandhalogenbonds AT yvesldory isomorphouscrystalsfromdiynesandbromodiynesinvolvedinhydrogenandhalogenbonds |